870723-88-9

Upstream product

• 109-04-6 2-bromo-pyridine 
• 3058-39-7 4-iodobenzonitrile 
• 1279130-08-3 2-[(4-methoxyphenyl)sulfinyl]pyridine 
• 1309446-75-0 4-(2-((4-methoxyphenyl)sulfinyl)pyridin-3-yl)benzonitrile 
• 31401-23-7 p-methoxybenzenesulfinyl chloride 

Relevant academic research and scientific papers

Difunctionalisation of arenes and heteroarenes by directed metallation and sulfoxide-magnesium exchange

The aryl sulfoxide moiety allows an expedient two-step difunctionalisation of readily available diaryl sulfoxides. Highly functionalised 1,2,4-trisubstituted arenes and difunctionalised heteroarenes (furans, thiophenes, benzofurans and pyridines) were prepared in a two-step sequence, triggered by an aryl sulfoxide group. In the first step, the sulfoxide moiety acts as a metallation-directing group, allowing smooth ortho-magnesiation with TMPMgCl.LiCl (TMP=tetramethylpiperidine). After a quenching reaction with an electrophile, the resulting sulfoxide is converted into a second magnesium reagent with iPrMgCl.LiCl (sulfoxide-magnesium exchange), which can be trapped with various electrophiles. Highly chemoselective TMPMgCl.LiCl and iPrMgCl.LiCl are compatible with a broad range of functional groups (e.g., F, Cl, CF 3, CN, CO2tBu, alkynyl, ethers, thioethers). Large-scale reactions (25-40 mmol) and the preparation of fully functionalised furans and thiophenes are also reported. Successful exchange: Highly functionalised 1,2,4-trisubstituted arenes and difunctionalised heteroarenes were prepared in a two-step sequence, triggered by an aryl sulfoxide group. The chemoselective reagents used, TMPMgCl.LiCl (TMP=tetramethylpiperidine) and iPrMgCl.LiCl, are compatible with a broad range of functional groups (see scheme; E=electrophile.)

BICYCLIC COMPOUNDS

The present invention is to provide a bicyclic compound represented by the following formula: wherein Ring Q is pyridine or pyrimidine; Ring A is benzene or a heterocyclic ring; G is Ring B optionally having a substituent(s) R3, or an amino optionally substituted by one or two selected from the group consisting of alkyl(s), aralkyl(s) and cycloalkyl(s); Ring B is benzene, a heterocyclic ring, a cycloalkane or a cycloalkene; R1 is a group selected from the following formulae: R2 and R3 may be the same or different from each other, and each is cyano, nitro, etc.; m is 0, 1 or 2; R4 is hydrogen, a halogen, etc.; and R5 and R6 may be the same or different from each other, and each is hydrogen, an optionally substituted alkyl, etc., or a pharmaceutically acceptable salt thereof, which is a large conductance calcium-activated K channel opener useful for treatment of pollakiuria, urinary incontinence, etc.